((2R,3R,4R,5S,6R)-4-Benzyloxy-2-benzyloxymethyl-6-ethynyl-5-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Base Information

Chemical Name:((2R,3R,4R,5S,6R)-4-Benzyloxy-2-benzyloxymethyl-6-ethynyl-5-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane
CAS No.:511511-32-3
Molecular Formula:C₂₉H₄₀O₅Si
Molecular Weight:496.719
Hs Code.:

Synonyms:((2R,3R,4R,5S,6R)-4-Benzyloxy-2-benzyloxymethyl-6-ethynyl-5-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

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Chemical Property of ((2R,3R,4R,5S,6R)-4-Benzyloxy-2-benzyloxymethyl-6-ethynyl-5-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

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Technology Process of ((2R,3R,4R,5S,6R)-4-Benzyloxy-2-benzyloxymethyl-6-ethynyl-5-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

There total 5 articles about ((2R,3R,4R,5S,6R)-4-Benzyloxy-2-benzyloxymethyl-6-ethynyl-5-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

: 511511-31-2
(2R,3S,4R,5R,6R)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-pyran-3-ol

: 74-88-4
methyl iodide

: 511511-32-3
((2R,3R,4R,5S,6R)-4-Benzyloxy-2-benzyloxymethyl-6-ethynyl-5-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;
DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 511511-32-3
((2R,3R,4R,5S,6R)-4-Benzyloxy-2-benzyloxymethyl-6-ethynyl-5-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / imidazole / dimethylformamide / 16 h / 60 °C

2: 100 percent / dimethyldioxirane / acetone; CH₂Cl₂ / 0.08 h / 0 °C

3: 75 percent / ZnCl₂ / tetrahydrofuran; various solvent(s) / 1 h / 0 - 20 °C

4: 93 percent / NaH / dimethylformamide / 1 h / 0 °C

With 1H-imidazole; 3,3-dimethyldioxirane; sodium hydride; zinc(II) chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2

Reference yield:

: 145852-76-2
3,6-di-O-benzyl-D-glucal

: 511511-32-3
((2R,3R,4R,5S,6R)-4-Benzyloxy-2-benzyloxymethyl-6-ethynyl-5-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / imidazole / dimethylformamide / 16 h / 60 °C

2: 100 percent / dimethyldioxirane / acetone; CH₂Cl₂ / 0.08 h / 0 °C

3: 75 percent / ZnCl₂ / tetrahydrofuran; various solvent(s) / 1 h / 0 - 20 °C

4: 93 percent / NaH / dimethylformamide / 1 h / 0 °C

With 1H-imidazole; 3,3-dimethyldioxirane; sodium hydride; zinc(II) chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1002/1099-0690(200212)2002:23<3954::AID-EJOC3954>3.0.CO;2-2